[1,1'-Biphenyl]-3-sulfonylchloride supplier

Name
3-PHENYLBENZENESULFONYL CHLORIDE
EINECS
CAS No. 65685-01-0
Article Data10
CAS DataBase
Density 1.321 g/cm³
Solubility
Melting Point 38-40 °C
Formula C₁₂H₉ClO₂S
Boiling Point 397.824 °C at 760 mmHg
Molecular Weight 252.721
Flash Point 194.397 °C
Transport Information
Appearance
Safety 26
Risk Codes 36
Molecular Structure
Hazard Symbols C
Synonyms 3-Phenylbenzenesulfonylchloride;Biphenyl-3-sulfonyl chloride;
PSA 42.52000
LogP 4.36190

Synthetic route

: 94306-39-5
[1,1'-biphenyl]-3-yl(benzyl)sulfane

: 65685-01-0
biphenyl-3-sulfonyl chloride

Conditions

Conditions	Yield
With N-chloro-succinimide; acetic acid In water at 20℃;	59%
With N-chloro-succinimide; acetic acid In water at 20℃;	59%

: 2113-57-7
3-bromobiphenyl

: 65685-01-0
biphenyl-3-sulfonyl chloride

Conditions

Conditions	Yield
With sulfuryl dichloride; tert.-butyl lithium In diethyl ether at -78 - 20℃; for 7h;	49%
In tetrahydrofuran
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 2: N-chloro-succinimide; acetic acid / water / 20 °C View Scheme

: 2113-57-7
3-bromobiphenyl

: 594-19-4
tert.-butyl lithium

: 65685-01-0
biphenyl-3-sulfonyl chloride

Conditions

Conditions	Yield
With sulfuryl dichloride In hexane; ethyl acetate	49%

: 2113-57-7
3-bromobiphenyl

: 65685-01-0
biphenyl-3-sulfonyl chloride

Conditions

Conditions	Yield
With sulfuryl dichloride; tert.-butyl lithium In hexane; ethyl acetate	49%

: 591-18-4
1-Bromo-3-iodobenzene

: 65685-01-0
biphenyl-3-sulfonyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 2 h / 90 °C / Inert atmosphere; Sealed tube 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 3: N-chloro-succinimide; acetic acid / water / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 2 h / 90 °C / Inert atmosphere; Sealed tube 2: N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 3: N-chloro-succinimide; acetic acid / water / 20 °C View Scheme

Yield

Multi-step reaction with 3 steps
1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 2 h / 90 °C / Inert atmosphere; Sealed tube
2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube
3: N-chloro-succinimide; acetic acid / water / 20 °C
View Scheme

Multi-step reaction with 3 steps
1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 2 h / 90 °C / Inert atmosphere; Sealed tube
2: N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube
3: N-chloro-succinimide; acetic acid / water / 20 °C
View Scheme

: 98-80-6
phenylboronic acid

: 65685-01-0
biphenyl-3-sulfonyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 2 h / 90 °C / Inert atmosphere; Sealed tube 2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 3: N-chloro-succinimide; acetic acid / water / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 2 h / 90 °C / Inert atmosphere; Sealed tube 2: N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 3: N-chloro-succinimide; acetic acid / water / 20 °C View Scheme

Yield

: 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)piperidine trifluoroacetic acid salt

: 65685-01-0
biphenyl-3-sulfonyl chloride

: C35H44N2O3S

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;	98%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 3-(4-(aminomethyl)benzyl)-7-ethyl-1H-purine-2,6(3H,7H)-dione trifluoroacetic acid salt

: N-(4-((7-ethyl-2,6-dioxo-1H-purin-3(2H,6H,7H)-yl)methyl)benzyl)-[1,1′-biphenyl]-3-sulfonamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 12h;	96%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 91569-33-4
(1,1′-biphenyl)-3-sulfonamide

Conditions

Conditions	Yield
With ammonium hydroxide In dichloromethane; water at 20℃; for 6.5h; Cooling with ice;	93%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 24313-88-0
3,4,5-Trimethoxyaniline

: 1311195-74-0
N-(3,4,5-trimethoxyphenyl)biphenyl-3-sulfonamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide	91.7%
With triethylamine In N,N-dimethyl-formamide	91.7%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 1481-11-4
N-methyl-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]aniline

: biphenyl-3-sulfonic acid methyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-amide

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In acetone at 60℃; for 24h;	90%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: C13H15N3O

: (biphenyl-3-yl)sulfonyl-(R)-phenylalanylaminocyclopropane nitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	89%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: C10H17N3O

: (biphenyl-3-yl)sulfonyl-(R)-leucylaminocyclopropane nitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	78%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 7795-52-0
(-)-alpha-Methyltryptamine

: (R)-N-(1-(1H-indol-3-yl)propan-2-yl)-[1,1'-biphenyl]-3-sulfonamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	77%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 65-49-6
4-Aminosalicylic acid

: 1353433-22-3
4-[(biphenyl-3-ylsulfonyl)amino]-2-hydroxybenzoic acid

Conditions

Conditions	Yield
With pyridine In dichloromethane at 60℃; for 4h;	74%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: (S)-2-amino-N-(1-cyanocyclopropyl)-3-phenylpropanamide

: (biphenyl-3-yl)sulfonyl-(S)-phenylalanylaminocyclopropane nitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	71%

: 540522-70-1
methyl 4-{3-[2-(2-aminoethyl)-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoate

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 1019217-38-9
methyl 4-[3-(1-benzhydryl-2-{2-[(1,1'-biphenyl-3-ylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)propyl]benzoate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water Schotten-Baumann reaction;	65%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 166964-09-6
4-chloro-3-methyl-5-amino isoxazole

: N-(4-chloro-3-methyl-5-isoxazolyl)-3-biphenylsulfonamide

Conditions

Conditions	Yield
	63%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 6-((2-chloro-6-fluorobenzyl)oxy)indoline

: 1-([1,1’-biphenyl]-3-ylsulfonyl)-6-((2-chloro-6-fluorobenzyl)oxy)indoline

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	63%

: 540522-69-8
methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate amine

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 1019216-96-6
methyl 4-[2-(1-benzhydryl-2-{2-[(1,1'-biphenyl-3-ylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethoxy]benzoate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water Schotten-Baumann reaction;	61%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: C15H21N3O

: (biphenyl-3-yl)sulfonyl-(S)-leucylphenylalanine nitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	58%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: N-(1-cyanocyclopropyl)-L-leucinamide

: (biphenyl-3-yl)sulfonyl-(S)-leucylaminocyclopropane nitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	51%

: 2103-99-3
4-(4-chlorophenyl)-2-thiazolamine

: 65685-01-0
biphenyl-3-sulfonyl chloride

: N-[4-(4-chlorophenyl)thiazol-2-yl]-3-phenylbenzenesulfonamide

Conditions

Conditions	Yield
With pyridine at 80℃; for 8h;	47%

: N-Boc-trans-1,4-bis(aminomethyl)cyclohexane

: 65685-01-0
biphenyl-3-sulfonyl chloride

: tert-butyl [(trans-4-{[(biphenyl-3-ylsulfonyl)amino]methyl}cyclohexyl)methyl]carbamate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	42%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 5'-amino-6'-chloro-N-methyl-[3,3'-bipyridine]-5-carboxamide

: 5’-([1,1'-biphenyl]-3-sulfonamido)-6'-chloro-N-methyl-[3,3'-bipyridine]-5-carboxamide

Conditions

Conditions	Yield
With pyridine at 20℃; for 6h; Inert atmosphere;	38%

: 111-26-2
hexan-1-amine

: 65685-01-0
biphenyl-3-sulfonyl chloride

: methyl 1-(3-(chloromethyl)phenyl)-5-((trans)-2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate

: 1-(3-((N-hexyl-[1,1'-biphenyl]-3-ylsulfonamido)methyl)phenyl)-5-((trans)-2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: hexan-1-amine; biphenyl-3-sulfonyl chloride With N-ethyl-N,N-diisopropylamine In acetonitrile for 0.0166667h; Stage #2: methyl 1-(3-(chloromethyl)phenyl)-5-((trans)-2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate With sodium hydride In acetonitrile; mineral oil at 140℃; for 0.0166667h; Microwave irradiation; Stage #3: With potassium hydroxide In water; acetonitrile; mineral oil Microwave irradiation;	32%

Yield

Stage #1: hexan-1-amine; biphenyl-3-sulfonyl chloride With N-ethyl-N,N-diisopropylamine In acetonitrile for 0.0166667h;
Stage #2: methyl 1-(3-(chloromethyl)phenyl)-5-((trans)-2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate With sodium hydride In acetonitrile; mineral oil at 140℃; for 0.0166667h; Microwave irradiation;
Stage #3: With potassium hydroxide In water; acetonitrile; mineral oil Microwave irradiation;

32%

...Expand

: 65685-01-0
biphenyl-3-sulfonyl chloride

: novenamine hydrochloride

: C31H32N2O11S

Conditions

Conditions	Yield
With pyridine at -40 - 23℃; for 12h; Inert atmosphere; Sealed tube;	32%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 33084-49-0
4-bromo-3-methyl-5-aminoisoxazole

: N-(4-bromo-3-methyl-5-isoxazolyl)-3-biphenylsulfonamide

Conditions

Conditions	Yield
	22%

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 124-41-4
sodium methylate

: biphenyl-3-sulfonic acid methyl ester

Conditions

Conditions	Yield
With methanol

: 39662-63-0
5-ethoxy-pyrrolidin-2-one

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 111711-71-8
1-(Biphenyl-3-sulfonyl)-5-ethoxy-pyrrolidin-2-one

Conditions

Conditions	Yield
With n-butyllithium 1.) THF, hexane, -70 deg C, 45 min, 2.) THF, hexane, -70 deg C, 2 h; Yield given. Multistep reaction;

: 19947-75-2
5-amino-3,4-dimethylisoxazol

: 65685-01-0
biphenyl-3-sulfonyl chloride

: N-(3,4-dimethyl-5-isoxazolyl)-3-biphenylsulfonamide

: 65685-01-0
biphenyl-3-sulfonyl chloride

: 3-(3-(S)-amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride

: 1027145-58-9
Biphenyl-3-sulfonic acid [(S)-1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-yl]-amide

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 2h; Condensation; amidation;

[1,1'-Biphenyl]-3-sulfonylchloride Specification

The IUPAC name of [1,1'-Biphenyl]-3-sulfonylchloride is 3-phenylbenzenesulfonyl chloride. With the CAS registry number 65685-01-0, it is also named as Biphenyl-3-sulfonyl chloride. In addition, its molecular formula is C₁₂H₉ClO₂S and its molecular weight is 252.72.

The other characteristics of [1,1'-Biphenyl]-3-sulfonylchloride can be summarized as: (1)ACD/LogP: 3.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.443; (4)ACD/LogD (pH 7.4): 3.443; (5)ACD/BCF (pH 5.5): 243.785; (6)ACD/BCF (pH 7.4): 243.785; (7)ACD/KOC (pH 5.5): 1779.204; (8)ACD/KOC (pH 7.4): 1779.204; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 42.52 Å²; (13)Index of Refraction: 1.596; (14)Molar Refractivity: 65.107 cm³; (15)Molar Volume: 191.374 cm³; (16)Polarizability: 25.81×10^-24cm³; (17)Surface Tension: 44.487 dyne/cm; (18)Density: 1.321 g/cm³; (19)Flash Point: 194.397 °C; (20)Enthalpy of Vaporization: 62.304 kJ/mol; (21)Boiling Point: 397.824 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: c1ccc(cc1)c2cccc(c2)S(=O)(=O)Cl
(2)InChI: InChI=1/C12H9ClO2S/c13-16(14,15)12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-9H
(3)InChIKey: LKSVJXWZVULUDA-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C12H9ClO2S/c13-16(14,15)12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-9H
(5)Std. InChIKey: LKSVJXWZVULUDA-UHFFFAOYSA-N

Product Name

3-PHENYLBENZENESULFONYL CHLORIDE

Synthetic route

[1,1'-Biphenyl]-3-sulfonylchloride Specification

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